title: Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization.
abstract: The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized lambda(5)-iodane reagent IBX (SIBX). (+)-Wasabidienone B1 was then converted into its congener (-)-wasabidienone B0 via an improved thermally induced ring-contracting isomerization reaction.
authors.affiliation: Institut des Sciences Moléculaires, CNRS-UMR 5255, Université de Bordeaux, Pessac Cedex, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Pouységu
authors.forename: Mélanie
authors.initials: M
authors.lastname: Marguerit
authors.forename: Julien
authors.initials: J
authors.lastname: Gagnepain
authors.forename: Gildas
authors.initials: G
authors.lastname: Lyvinec
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Eatherton
authors.forename: Stéphane
authors.initials: S
authors.lastname: Quideau
mesh_terms: D002384:Catalysis; D006900:Hydroxylation; D007202:Indicators and Reagents / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D007536:Isomerism; D007783:Lactones / Q000138:chemical synthesis*; D010636:Phenols / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis*
chemical_list: D007202:Indicators and Reagents; D007462:Iodobenzenes; D007783:Lactones; D010636:Phenols; D011809:Quinones; C533651:wasabidienone B0; C533650:wasabidienone B1; C476101:o-iodoxybenzoic acid